Editing Nucleophile (section)

===Ambident nucleophile===
An '''ambident nucleophile''' is one that can attack from two or more places, resulting in two or more products. For example, the [[thiocyanate]] ion (SCN<sup>−</sup>) may attack from either the sulfur or the nitrogen. For this reason, the [[SN2 reaction|S<sub>N</sub>2 reaction]] of an alkyl halide with SCN<sup>−</sup> often leads to a mixture of an alkyl thiocyanate (R-SCN) and an alkyl [[isothiocyanate]] (R-NCS). Similar considerations apply in the [[Kolbe nitrile synthesis]].{{cn|date=March 2024}}